Process of making camphene.



UNITED STAT1 PATENT OFFICE.

CHARLES WEIZMANN, OF MANCHESTER, ENGLAND, ASSIGNOR TO THE CLAYTON ANILINE COMPANY, LIMITED, OF MANCHESTER, ENGLAND.

PROCESS OF MAKING CAMPHENE.

No. seaeea Specification of Letters Patent.

Patented Aug. a5, 1908.

To all whom it may concern:

Be it known that I, CHARLES WEIZ- MANN, of Manchester, England, have invented certain new and useful Improvements in I parts by weight of pinene hydrochlorid, in

the Manufacture of Camphene, of which the following is a specification.

It is known that camphenecan be produced by heating pinene hydrochlorid with certain organic bases, but hitherto only primary and secondary organic bases have been employed for the purpose, such, for example, as methyl amin and anilin, both of which, according to Briihl (see Ber. XXV 146) give very unsatisfactory results. 'It'has also been proposed to use cyclic bases, such as piperidin and piperazin (see the specification of British Letters Patent No. 26620 A. D. 1901,) and it is stated that, when these are employed, a yield of eighty per cent. of camphene can be obtained.

I have found that by heating pinene hydrochlorid with a heterocyclic base of the pyridin type, such, for example, as pyridin, or quinolin, yields of from eighty-five to ninety per cent. of camphene can be obtained, and this invention consists in the use of such tertiary bases for the purpose.

The following are examples of manners in which this invention can be performed, but I do not limit myself to the details given in these examples:

Example I. A solution of 200 parts by weight of pinene hydrochlorid, in four hundred and fifty parts, by weight, of quinolin, is boiled, for about seven hours and the product, which is the result of the reaction which takes place, is acidified by sulfuric acid and the camphene is distilled off bymeans of steam and rectified if necessary. The product is rectified by distilling the. crude camphene obtained and freezing it out afterwards.

The eamphene solidifies, and can be filtered off or passed through a hydro-extractor.

Example II. A solution of two hundred four hundred parts by weight of pyridin oils, boiling from 180 to 200 centigrade, (I take pyridin oils which begin to boil at 180) is boiled for about ten hours. The calnphene which is produced, as the result of the reaction, is then isolated in the manner described in the foregoing Example I.

The equation is as follows:

C H Cl C H N C H C H NCl pinene camphenc. hydrochlorid.

At the high temperature (.180200) a molecular transposition takes place, and the pinene molecule is transformed into the camphene molecule.

Pyridin oils boiling from 180 to 200 are mixtures of pyridin and pyridin homologues, such as obtained on distillation of bone-oil or coal tar bases. I take the fraction which boils between 180 and 200.

Having now particularly described the nature of my said invention, and in what manner the same is to be performed, I declare that what I claim is A process of making camphene by boiling pinene hydrochlorid with a tertiary heterocyclic base of the pyridin type, acidifying the resultant mixture and distilling it in steam.

In testimony whereof I have aflixed my Witnesses:

ERNOLD SIMPsoN MOSELEY, MALCOLM SMETHURST. 

